Nymphaeol A

Details

• Internal ID: 84a5fac1-b412-458e-987d-a03600ec8adf
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC(=C(C=C3)O)O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC(=C(C=C3)O)O)O)/C)C
• InChI: InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)7-9-17-19(27)12-23-24(25(17)30)21(29)13-22(31-23)16-8-10-18(26)20(28)11-16/h5,7-8,10-12,22,26-28,30H,4,6,9,13H2,1-3H3/b15-7+/t22-/m0/s1
• InChI Key: XCYSQFHYFNWYFP-CEMXSPGASA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.45
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• Propolin C
• CHEBI:66640
• 73676-38-7
• 6-geranyl-3',4',5,7-tetrahydroxyflavanone
• (2S)-2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
• CHEMBL223256
• SCHEMBL7795014
• SCHEMBL16105856
• BDBM50380205
• (2S)-2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• Q27135257
• 2-(3,4-dihydroxyphenyl)-6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
• 4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-(3,7-dimethyl-2,6-octadienyl)-2,3-dihydro-5,7-dihydroxy-, (2S)-
• InChI=1/C25H28O6/c1-14(2)5-4-6-15(3)7-9-17-19(27)12-23-24(25(17)30)21(29)13-22(31-23)16-8-10-18(26)20(28)11-16/h5,7-8,10-12,22,26-28,30H,4,6,9,13H2,1-3H3/b15-7+/t22-/m0/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9501	95.01%
Caco-2	-	0.7930	79.30%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	0.5741	57.41%
OATP1B1 inhibitior	+	0.9081	90.81%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8518	85.18%
P-glycoprotein inhibitior	+	0.6249	62.49%
P-glycoprotein substrate	-	0.8118	81.18%
CYP3A4 substrate	+	0.5850	58.50%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.8017	80.17%
CYP3A4 inhibition	-	0.6358	63.58%
CYP2C9 inhibition	-	0.6077	60.77%
CYP2C19 inhibition	+	0.5246	52.46%
CYP2D6 inhibition	-	0.8219	82.19%
CYP1A2 inhibition	+	0.7028	70.28%
CYP2C8 inhibition	-	0.5923	59.23%
CYP inhibitory promiscuity	-	0.5548	55.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7492	74.92%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.7159	71.59%
Skin irritation	-	0.7352	73.52%
Skin corrosion	-	0.9308	93.08%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6432	64.32%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7765	77.65%
Acute Oral Toxicity (c)	III	0.4062	40.62%
Estrogen receptor binding	+	0.9178	91.78%
Androgen receptor binding	+	0.7613	76.13%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.8033	80.33%
Aromatase binding	+	0.6048	60.48%
PPAR gamma	+	0.8524	85.24%
Honey bee toxicity	-	0.7964	79.64%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	7200 nM	IC50	PMID: 22445674
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	50 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.45%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.89%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	93.42%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.43%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.70%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.20%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.58%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.29%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.54%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.49%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.08%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.59%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.37%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.69%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.39%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.53%	90.00%

Plants that contains it

• Bobgunnia madagascariensis
• Calodendrum capense
• Croton caudatus
• Elaeocarpus fuscoides
• Hernandia nymphaeifolia
• Jacobaea adonidifolia
• Macaranga alnifolia
• Macaranga tanarius
• Meconopsis horridula
• Oxera splendida
• Paulownia tomentosa
• Schizolaena hystrix
• Sophora flavescens
• Stevia eupatoria
• Vitex pinnata

Cross-Links

• PubChem: 639465
• NPASS: NPC213896
• ChEMBL: CHEMBL223256
• LOTUS: LTS0012906
• wikiData: Q27135257